WO2015089853A1 - 蓝色荧光有机材料及有机发光二极管面板 - Google Patents
蓝色荧光有机材料及有机发光二极管面板 Download PDFInfo
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- WO2015089853A1 WO2015089853A1 PCT/CN2013/090209 CN2013090209W WO2015089853A1 WO 2015089853 A1 WO2015089853 A1 WO 2015089853A1 CN 2013090209 W CN2013090209 W CN 2013090209W WO 2015089853 A1 WO2015089853 A1 WO 2015089853A1
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- Prior art keywords
- blue fluorescent
- organic material
- fluorescent organic
- group
- light emitting
- Prior art date
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- 239000011368 organic material Substances 0.000 title claims abstract description 24
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000005577 anthracene group Chemical group 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 230000005525 hole transport Effects 0.000 claims description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000007772 electrode material Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006612 decyloxy group Chemical group 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000463 material Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- FIHILUSWISKVSR-UHFFFAOYSA-N 3,6-dibromo-9h-carbazole Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3NC2=C1 FIHILUSWISKVSR-UHFFFAOYSA-N 0.000 description 2
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- ONFSYSWBTGIEQE-UHFFFAOYSA-N n,n-diphenyl-4-[2-[4-[2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]ethenyl]aniline Chemical compound C=1C=C(C=CC=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ONFSYSWBTGIEQE-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- BMQDAIUNAGXSKR-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl)oxyboronic acid Chemical compound CC(C)(O)C(C)(C)OB(O)O BMQDAIUNAGXSKR-UHFFFAOYSA-N 0.000 description 1
- 0 *(c(ccc(-c1c(cccc2)c2ccc1)c1)c1-c1c2)c1ccc2-c1cccc2c1cccc2 Chemical compound *(c(ccc(-c1c(cccc2)c2ccc1)c1)c1-c1c2)c1ccc2-c1cccc2c1cccc2 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- -1 2,7-dibromo-9,9-diethylanthracene Chemical compound 0.000 description 1
- QPTWWBLGJZWRAV-UHFFFAOYSA-N 2,7-dibromo-9-H-carbazole Natural products BrC1=CC=C2C3=CC=C(Br)C=C3NC2=C1 QPTWWBLGJZWRAV-UHFFFAOYSA-N 0.000 description 1
- SEVBQRQACXXUJG-UHFFFAOYSA-N 2-(4-bromophenyl)quinoline Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C=CC=C2)C2=N1 SEVBQRQACXXUJG-UHFFFAOYSA-N 0.000 description 1
- JZKFQOQTRQVMAU-UHFFFAOYSA-N 3,6-dinaphthalen-1-yl-9h-carbazole Chemical compound C1=CC=C2C(C3=CC=C4NC5=CC=C(C=C5C4=C3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 JZKFQOQTRQVMAU-UHFFFAOYSA-N 0.000 description 1
- FCTCELFSOMQGDE-UHFFFAOYSA-N 3,6-dinaphthalen-1-yl-9h-fluorene Chemical compound C1=CC=C2C(C3=CC=C4CC5=CC=C(C=C5C4=C3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 FCTCELFSOMQGDE-UHFFFAOYSA-N 0.000 description 1
- PPCCJKDGLHFCOI-UHFFFAOYSA-N CCC1(CC)c(cc(cc2)[BrH]C)c2-c(cc2)c1cc2Br Chemical compound CCC1(CC)c(cc(cc2)[BrH]C)c2-c(cc2)c1cc2Br PPCCJKDGLHFCOI-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PMFLKFYMOPZDJD-UHFFFAOYSA-N O1CCOCC1.O1C=COC=C1 Chemical compound O1CCOCC1.O1C=COC=C1 PMFLKFYMOPZDJD-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-O diphenylphosphanium Chemical compound C=1C=CC=CC=1[PH2+]C1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-O 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002923 oximes Chemical group 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/191—Deposition of organic active material characterised by provisions for the orientation or alignment of the layer to be deposited
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/611—Charge transfer complexes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Definitions
- This invention relates to a blue fluorescent organic material, and more particularly to a blue fluorescent organic material for use in an emissive layer of an organic light emitting diode panel. Background technique
- blue fluorescent material such as DSA-Ph, l-4-di-[ 4-(N,N-di-phenyl)amino]styryl-benzene
- DSA-Ph DSA-Ph, l-4-di-[ 4-(N,N-di-phenyl)amino]styryl-benzene
- DSA-Ph DSA-Ph, l-4-di-[ 4-(N,N-di-phenyl)amino]styryl-benzene
- the present invention provides a blue fluorescent organic material in which an electron-deficient group is introduced in a molecular structure to solve the problems of the prior art and achieve a color purity of deep blue light to provide an all-natural color display. Effect.
- the present invention provides a blue fluorescent organic material excellent in overall performance, including light-emitting efficiency, charge injection/transport characteristics, stability, color purity, and the like.
- An object of the present invention is to provide an application of the above-described blue fluorescent organic material in an organic light emitting diode, which can achieve an effect closer to an all natural color display.
- an embodiment of the present invention provides a blue fluorescent organic material comprising an organic compound having the structure of the following formula (I): Formula (I)
- R is alkyl with the dC 2Q, the embankment dC 2Q dC 2Q group or aromatic group-containing substituent; eight 11 ⁇ 1, a phenyl group, fused ring aromatic group or a substituted phenyl and substituted condensed polycyclic aromatic group 2 is:
- the ⁇ ⁇ has a naphthalene ring, an anthracene ring or a phenanthrene ring structure.
- the ⁇ ⁇ is one of the substituents having the following structure
- an organic light emitting diode panel including an upper electrode, a lower electrode, a light emitting layer, and a conductive layer, wherein the light emitting layer comprises a blue fluorescent organic material as described above.
- the upper electrode material is indium tin oxide.
- the lower electrode is a metal cathode.
- the conductive layers comprise an electron transport layer or a hole transport layer.
- Fig. 1 is a view showing the ultraviolet-visible absorption spectrum and photoluminescence spectrum of a solution (toluene, 10-5 mol/liter) of an organic compound of the first embodiment of the present invention and a film.
- Fig. 2 is a differential scanning calorimetry (DSC) curve of the organic compound of the first embodiment of the present invention.
- Fig. 3 is a graph showing the thermogravimetric analysis (TGA) of the organic compound of the first embodiment of the present invention.
- Fig. 4 is a view showing an organic compound formula 1 for use in an organic light emitting diode panel according to a second embodiment of the present invention. detailed description
- the blue fluorescent organic material of the first embodiment of the present invention mainly comprises a structure having the following formula (I)
- the ⁇ ⁇ has a naphthalene ring, an anthracene ring or a phenanthrene ring structure, and may be, for example, one of the substituents of the following structures
- the preparation method of the blue fluorescent organic material of the formula 1 is as follows:
- the quantum efficiency of the thin film fluorescence was measured to be 77.9%.
- the photoluminescence is located in the deep blue region.
- DSC differential scanning calorimetry
- TGA thermogravimetric analysis
- the OLED panel of the second embodiment of the present invention mainly includes an upper electrode 1, a lower electrode 2, an illuminating layer 3, and at least one conductive layer 4, wherein the luminescent layer includes A blue fluorescent organic material as described above.
- the material of the upper electrode 1 may be indium tin oxide having semiconductor characteristics
- the lower electrode 2 is a metal cathode
- the conductive layers 4 may include an electron transport layer or a hole transport layer.
- the light-emitting layer 3 and the conductive layer 4 may be stacked between the upper electrode 1 and the lower electrode 2 to form a sandwich structure.
- the light-emitting layer formed by the blue fluorescent organic material emits deep blue light, so that the organic light-emitting diode panel can exhibit an effect close to an all-natural color.
- the blue fluorescent organic material provided according to the present invention has the following advantages:
- the film has high fluorescence efficiency and can effectively inhibit fluorescence quenching; (3) having a Donor-Acceptor structure, that is, a mixture of electron-donating units and electron-receiving units in a molecular structure, which facilitates the balance of carrier transport;
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Manufacturing & Machinery (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Indole Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016535166A JP6250811B2 (ja) | 2013-12-16 | 2013-12-23 | 青色蛍光有機材料及びその有機発光ダイオードパネル |
| KR1020167014556A KR101860456B1 (ko) | 2013-12-16 | 2013-12-23 | 청색 형광 유기 물질 및 유기 발광 다이오드 패널 |
| GB1607988.1A GB2534106B (en) | 2013-12-16 | 2013-12-23 | Blue fluorescent organic material and organic light emitting diode panel thereof |
| US14/235,800 US9059413B1 (en) | 2013-12-23 | 2013-12-23 | Blue fluorescent organic material and organic light emitting diode panel thereof |
| EA201691086A EA029982B1 (ru) | 2013-12-16 | 2013-12-23 | Синий флуоресцентный органический материал и органическая светодиодная панель из него |
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| CN201310689881.8A CN103666459B (zh) | 2013-12-16 | 2013-12-16 | 蓝色荧光有机材料及其有机发光二极管面板 |
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| CN101392174A (zh) * | 2008-10-27 | 2009-03-25 | 华南理工大学 | 可溶性电致绿光有机分子玻璃材料及其制备方法与应用 |
| KR20110079402A (ko) * | 2009-12-31 | 2011-07-07 | (주)씨에스엘쏠라 | 유기 광소자 및 이를 위한 유기 광합물 |
| CN103221406A (zh) * | 2010-09-17 | 2013-07-24 | 罗门哈斯电子材料韩国有限公司 | 新有机电致发光化合物和使用该化合物的有机电致发光器件 |
| CN103435597A (zh) * | 2013-09-04 | 2013-12-11 | 中国科学院理化技术研究所 | 1,3,5-三嗪衍生物及其在白光有机电致发光二极管中的应用 |
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| JP4427947B2 (ja) * | 2002-11-18 | 2010-03-10 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
| JP4585786B2 (ja) * | 2004-04-01 | 2010-11-24 | キヤノン株式会社 | 発光素子及び表示装置 |
| GB0600249D0 (en) * | 2006-01-06 | 2006-02-15 | Isis Innovation | Branched compounds and their use in sensors |
| KR101125683B1 (ko) * | 2010-06-21 | 2012-03-27 | 주식회사 이엘엠 | 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자 |
| JP5981440B2 (ja) * | 2011-10-19 | 2016-08-31 | 出光興産株式会社 | カルバゾール系重合体とそれを用いた有機エレクトロルミネッセンス素子 |
| KR102122453B1 (ko) * | 2013-02-28 | 2020-06-15 | 삼성디스플레이 주식회사 | 유기 발광 장치 |
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- 2013-12-16 CN CN201310689881.8A patent/CN103666459B/zh not_active Expired - Fee Related
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| CN101392174A (zh) * | 2008-10-27 | 2009-03-25 | 华南理工大学 | 可溶性电致绿光有机分子玻璃材料及其制备方法与应用 |
| KR20110079402A (ko) * | 2009-12-31 | 2011-07-07 | (주)씨에스엘쏠라 | 유기 광소자 및 이를 위한 유기 광합물 |
| CN103221406A (zh) * | 2010-09-17 | 2013-07-24 | 罗门哈斯电子材料韩国有限公司 | 新有机电致发光化合物和使用该化合物的有机电致发光器件 |
| CN103435597A (zh) * | 2013-09-04 | 2013-12-11 | 中国科学院理化技术研究所 | 1,3,5-三嗪衍生物及其在白光有机电致发光二极管中的应用 |
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Also Published As
| Publication number | Publication date |
|---|---|
| CN103666459B (zh) | 2015-01-21 |
| GB2534106B (en) | 2021-03-24 |
| GB201607988D0 (en) | 2016-06-22 |
| EA201691086A1 (ru) | 2016-11-30 |
| GB2534106A (en) | 2016-07-13 |
| KR20160068983A (ko) | 2016-06-15 |
| EA029982B1 (ru) | 2018-06-29 |
| CN103666459A (zh) | 2014-03-26 |
| JP6250811B2 (ja) | 2017-12-20 |
| JP2016540079A (ja) | 2016-12-22 |
| KR101860456B1 (ko) | 2018-05-23 |
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